The Second City is throwing the ultimate comedy party to celebrate 65 years of legendary laughs! The Best of The Second City: 65 Years of Funny brings together hilarious songs, unforgettable characters, and iconic sketches written for our stages by comedy greats like Tina Fey, Bill Murray, Catherine O’Hara, Keegan-Michael Key, Stephen Colbert, and so many more. Now, these classics are reimagined and brought to life by the funniest live comedy performers working today. Buckle up for a high-energy rollercoaster through six and a half decades of revolutionary satire and groundbreaking improv comedy.

Whether you’re a die-hard fan or discovering Second City for the first time, this is your chance to be part of the cutting-edge comedy tradition that’s been setting the bar for over half a century. Join us and see why The Second City is the past, present, and future of comedy.

Close Quarters is an improvised comedy where every scene unfolds just a wall, hallway, or whisper away. Set in one shared location, this fast-paced, character-driven show follows multiple storylines that collide, overlap, and hilariously unravel in real time. Directed by an ensemble member of the original production, Close Quarters honors its origins while showcasing a new cast of sharp, fearless improvisers. Come see how close things can really get.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo

Close Quarters is an improvised comedy where every scene unfolds just a wall, hallway, or whisper away. Set in one shared location, this fast-paced, character-driven show follows multiple storylines that collide, overlap, and hilariously unravel in real time. Directed by an ensemble member of the original production, Close Quarters honors its origins while showcasing a new cast of sharp, fearless improvisers. Come see how close things can really get.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo

Close Quarters is an improvised comedy where every scene unfolds just a wall, hallway, or whisper away. Set in one shared location, this fast-paced, character-driven show follows multiple storylines that collide, overlap, and hilariously unravel in real time. Directed by an ensemble member of the original production, Close Quarters honors its origins while showcasing a new cast of sharp, fearless improvisers. Come see how close things can really get.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

Sketch Playlist is a weekly sketch show that will feature brand-new material written and performed by the best and the brightest up-and-coming sketch writers and performers in Chicago. Every week, you'll see an all-new sketch show featuring all-new material - written and performed by a rotating Sketch Playlist team.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo

Annoyance founder Mick Napier created the Trigger Happy form out of a desire to make improv look as slick and beautifully put together as a scripted show. Through a language invisible to the audience, the fully improvised show magically comes to life. There is truly nothing else like it. An Annoyance Signature Improv show.

Flamboyant Attachment is a fast-paced, original sketch revue that dives headfirst into relationships, rejection, and the beautiful chaos of human connection. Five performers unravel a whirlwind of scenes, characters, and improv that's equal parts innovative, joyful, and absurd. Flat-out hilarious — no strings attached.

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

Sketch Playlist is a weekly sketch show that will feature brand-new material written and performed by the best and the brightest up-and-coming sketch writers and performers in Chicago. Every week, you'll see an all-new sketch show featuring all-new material - written and performed by a rotating Sketch Playlist team.

Flamboyant Attachment is a fast-paced, original sketch revue that dives headfirst into relationships, rejection, and the beautiful chaos of human connection. Five performers unravel a whirlwind of scenes, characters, and improv that's equal parts innovative, joyful, and absurd. Flat-out hilarious — no strings attached.

Flamboyant Attachment is a fast-paced, original sketch revue that dives headfirst into relationships, rejection, and the beautiful chaos of human connection. Five performers unravel a whirlwind of scenes, characters, and improv that's equal parts innovative, joyful, and absurd. Flat-out hilarious — no strings attached.

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo.